Volume 59, Issue 6 pp. 2338-2343
Communication

1,1-Diphenylvinylsulfide as a Functional AIEgen Derived from the Aggregation-Caused-Quenching Molecule 1,1-Diphenylethene through Simple Thioetherification

Bo-Wen Wang

Bo-Wen Wang

School of Chemistry, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, 510006 P. R. China

These authors contributed equally to this work.

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Kai Jiang

Kai Jiang

School of Chemistry, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, 510006 P. R. China

Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 P. R. China

These authors contributed equally to this work.

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Dr. Jian-Xiao Li

Dr. Jian-Xiao Li

Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 P. R. China

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Dr. Shi-He Luo

Dr. Shi-He Luo

School of Chemistry, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, 510006 P. R. China

Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 P. R. China

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Prof. Dr. Zhao-Yang Wang

Corresponding Author

Prof. Dr. Zhao-Yang Wang

School of Chemistry, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou, 510006 P. R. China

Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 P. R. China

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Prof. Dr. Huan-Feng Jiang

Corresponding Author

Prof. Dr. Huan-Feng Jiang

Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640 P. R. China

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First published: 25 November 2019
Citations: 92

Graphical Abstract

A simple thioetherification between 1,1-diphenylethene as an aggregation-induced emission (AIE)-imparting unit and sodium sulfinates provides a new route for the conversion of compounds with aggregation-caused quenching (ACQ) properties into AIE luminogens. This reaction delivers up to 99 % yield under mild conditions without additional oxidant, and gives access to novel trisubstituted-ethene-type AIEgens with potential for use in sensing applications.

Abstract

An efficient and readily scalable thioetherification between 1,1-diphenylethene (DPE) and sodium arylsulfinate was developed for the synthesis of 1,1-diphenylvinylsulfide (DPVS) with the yield up to 99 %. The photophysical properties of DPVS show that the introduction of arylsulfenyl groups onto the parent molecule DPE makes DPVS a novel type of aggregation-induced emission (AIE) luminogen (AIEgen) with large Stoke's shift (up to 188 nm). These DPVS possess AIE properties due to restriction of intramolecular motions (RIM), as demonstrated by crystal structure analysis. Importantly, the AIE performance of DPVS can be applied to sense the nitroaromatic explosive picric acid in aqueous systems through a “turn-off” response.

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